Issue 5, 2014

Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

Abstract

The central component of one of the most studied programmable molecular switches reported by Stoddart and Heath is a [2]rotaxane, which consists of a cyclobis(paraquat-p-phenylene) shuttle (CBPQT4+)(PF6)4 (the ring) encircling a finger and moving between two molecular stations, tetrathiafulvalene (TTF) and 1,5-dioxynaphthalene (DNP). In order to employ ESR spectroscopy for understanding the mechanism of this switch, we report here the synthesis and characterization of [2]rotaxanes having persistent nitroxide radicals as the stopper units and TTF or DNP as molecular stations. Isolation of the rotaxanes was successful when bulky nitroxide radicals containing cyclohexyl substituents at 2 and 6 positions of the piperidine-N-oxyl ring were used as terminal stoppers.

Graphical abstract: Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

Supplementary files

Article information

Article type
Research Article
Submitted
04 جمادى الأولى 1435
Accepted
26 جمادى الأولى 1435
First published
26 جمادى الأولى 1435

Org. Chem. Front., 2014,1, 477-483

Synthesis and characterization of spin-labelled [2]rotaxanes containing tetrathiafulvalene and 1,5-dioxynaphthalene molecular stations

R. Manoni, F. Romano, C. Casati, P. Franchi, E. Mezzina and M. Lucarini, Org. Chem. Front., 2014, 1, 477 DOI: 10.1039/C4QO00065J

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